Water → 4-(2-Methoxy-4-nitrophenyl)but-3-en-2-ol

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[CH:12]=[CH:13][C:14](=[O:16])[CH3:15].[BH4-].[Na+].O>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[CH:12]=[CH:13][CH:14]([OH:16])[CH3:15]

Participants

Procedure

To a suspension of 4-(2-methoxy-4-nitrophenyl)but-3-en-2-one (12.2 g; 55.2 mmol) in 150 mL of ethanol at rt was added NaBH4 (2.30 g; 60.7 mmol) over 5 minutes. The suspension was stirred at rt for 1 h, diluted with 1M NaHPO4 (˜60 mL) followed by water (100 mL) and concentrated under reduced pressure to remove ethanol. After extracting the aqueous residue with CH2Cl2, the organic layer was washed with water and brine, dried over anhydrous MgSO4, filtered. Concentration of the filtrate under reduced pressure afforded 12.3 g (100%) of the title compound as a dark, red gum. HPLC (Method #1) 3.68 min retention time, (50%); MS (ES): m/z 206 [M−OH]+.